Structures of new beta-carboline-type alkaloids with antiallergic effects from Stellaria dichotoma(1,2)

Journal of Natural Products
Bohang SunMasayuki Yoshikawa

Abstract

The aqueous ethanolic extract from the roots of Stellaria dichotoma showed an antiallergic effect on ear passive cutaneous anaphylaxis (PCA) reaction in mice (in vivo) and inhibitory activity on the release of beta-hexosaminidase in RBL-2H3 cells (in vitro). From the aqueous ethanolic extract, new beta-carboline-type alkaloids, dichotomines A (1), B (2), C (3), and D (4) and dichotomides I (5) and II (6), were isolated. The structures of the new constituents (1-6) were determined on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method. The effects of the isolated constituents on the release of beta-hexosaminidase in RBL-2H3 cells were examined, and 3 was found to show inhibitory activity (IC(50) = 62 microM). Moreover, 3 also inhibited the releases of antigen-IgE-mediated TNF-alpha and IL-4 (19 and 15 microM, respectively) in RBL-2H3 cells, both of which participate in the late phase of type I allergic reactions.

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Citations

Jan 22, 2013·Journal of Natural Products·Robert J R JaegerPeter Spiteller
Nov 29, 2005·Natural Product Reports·Tomomi Kawasaki, Kazuhiro Higuchi
May 3, 2006·Chemical & Pharmaceutical Bulletin·Haihui XieMasayuki Yoshikawa
Feb 2, 2008·Chemical & Pharmaceutical Bulletin·Kana OmuraSatoshi Hibino
Feb 9, 2012·Bioscience, Biotechnology, and Biochemistry·Myun-Ho BangSeun-Ah Yang
Jan 3, 2015·Natural Product Research·Yangmei ZhangLingyi Kong
Jul 16, 2016·Journal of Natural Products·Toshio MorikawaTakashi Nakayama
Apr 1, 2017·The Journal of Organic Chemistry·C Henrique Alves EstevesTimothy J Donohoe
Aug 16, 2006·Bioorganic & Medicinal Chemistry·Masayuki YoshikawaOsamu Muraoka
Feb 3, 2016·Chemical & Pharmaceutical Bulletin·Hisashi MatsudaMasayuki Yoshikawa
Aug 2, 2012·Organic & Biomolecular Chemistry·Sandra MedinaJavier Pérez-Castells
Nov 25, 2020·Antonie van Leeuwenhoek·Mohandas DhaneeshaThavarool Puthiyedathu Sajeevan
Nov 1, 2005·Environmental Toxicology and Pharmacology·K G Nevin, P L Vijayammal
Nov 26, 2010·Journal of Natural Products·Yuh-Fung ChenTian-Shung Wu

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